FTIR spectra of 2,3-dihydroquinolin-4-one Analogues

dc.contributor.other Rajput, Santoshkumar en_US
dc.contributor.other Kumar, Naresh en_US 2021-11-26T10:32:42Z 2021-11-26T10:32:42Z 2013 en_US
dc.description.abstract 2,3-dihydroquinolin-4-one Analogues were characterised using FTIR spectroscopy- The FTIR spectra were acquired using a Perkin Elmer FTIR instrument equipped with a Universal-ATR accessory where sample are pressed on a diamond crystal. Measurement parameters are contained within the data. en_US
dc.language English
dc.language.iso EN en_US
dc.rights CC-BY-NC-ND en_US
dc.rights.uri en_US
dc.subject.other 2,3-dihydroquinolin-4-one Analogues en_US
dc.title FTIR spectra of 2,3-dihydroquinolin-4-one Analogues en_US
dc.type Dataset en_US
dcterms.accessRights metadata only access
dcterms.accrualMethod en_US
dcterms.rightsHolder Copyright 2012, University of New South Wales en_US
dspace.entity.type Dataset en_US
unsw.contributor.leadChiefInvestigator Moran, Grainne en_US
unsw.contributor.researchDataCreator Gloria, Danmar en_US
unsw.coverage.temporalFrom 2011-06-15 en_US
unsw.coverage.temporalTo 2011-06-15 en_US For access to this data, please contact: Santosh Rajput Analytical Centre Lab 333 University of New South Wales, NSW Australia 2052 Email: en_US
unsw.description.storageplace UNSW Australia, Sydney NSW 2052 en_US
unsw.relation.OriginalPublicationAffiliation Gloria, Danmar, Division of Human Resources, Operations Division, en_US
unsw.relation.OriginalPublicationAffiliation Rajput, Santoshkumar, , This record is inactive, as the person is not currently at UNSW., en_US
unsw.relation.OriginalPublicationAffiliation Kumar, Naresh, School of Chemistry, Faculty of Science, en_US
unsw.relation.OriginalPublicationAffiliation Moran, Grainne, D PVC Research Infrastruture, Research & Enterprise, en_US
unsw.relation.faculty Science
unsw.relation.faculty Other UNSW
unsw.relation.projectDesc The primary aim of the project was to investigate various methodologies for the synthesis of aza-analogues of isoflavones, or 4-quinolones, and their reduced analogues with an oxygenated pattern that is present in naturally occurring flavonoids. A series of 3-aryl-5,7-dimethoxyquinolin-4-ones was synthesized by the reaction of 3,5-dimethoxyaniline with ?-aryl-?-ketoesters, giving enamino esters which were then converted to the corresponding 4-quinolones by thermal cyclization. The reduced 2,3-dihydroquinolin-4-one analogues were synthesized by the reaction of 3,5-dimethoxyaniline with ?-aryl-?-ketoesters in the presence of sodium cyanoborohydride, followed by amino group protection and ester hydrolysis. The resulting acids were then cyclized and deprotected to give the desired 2,3-dihydroquinolin-4-ones. The previously unreported 4-arylazaisoflavans were synthesized via two approaches. In the first approach, a Grignard reaction was performed on the carbonyl group of the 2,3-dihydroquinolin-4-ones, and the resulting alcohol was dehydrated and hydrogenated to give the fully reduced ring system, with a cis arrangement of substituents. In the other approach, the carbonyl group of 2,3-dihydroquinoline was reduced to an alcohol, which was then reacted with various nucleophiles. This approach gave the corresponding 4-aryl and 4-heteroarylazaisoflavan ring systems with a trans arrangement of substituents. The pyrrolo[3,2,1-ij]quinolin-6-one ring system was synthesized from 4-quinolones. The reaction of ?-bromo-acetophenones with 4-quinolones gave the corresponding quinolinoketones which on acid catalyzed cyclization gave the desired pyrroloquinolin-6-one. Reduction of pyrroloquinolin-6-ones with lithium aluminium hydride yielded the corresponding dihydroquinolin-6-ones. Selective demethylation of the C5-methoxy group in the synthesized 4-quinolones, 2,3-dihydroquinolin-4-ones and pyrroloquinolones was performed using cerium chloride and sodium iodide. Similar reactions with borontribromide gave dihydroxy analogues of 2,3-dihydroquinolin-4-one but was found to only selectively demethylate 4-arylazaisoflavans at C5. Dimethoxyquinolones also underwent Mannich reaction at C8 with primary amines and amino acid esters to give quinazolones. en_US
unsw.relation.projectEndDate 2012-12-31 en_US
unsw.relation.projectTitle Synthesis of novel heterocyclic analogues of isoflavones en_US School of Chemistry Mark Wainwright Analytical Centre
unsw.subject.fieldofresearchcode 030101 Analytical Spectrometry en_US
unsw.subject.fieldofresearchcode 030503 Organic Chemical Synthesis en_US
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